Palladium complexes derived from benzoylthiourea ligands: Synthesis, crystal structure, and catalytic application in Suzuki C–C coupling reactions. (15th July 2021)

• Record Type: Journal Article
• Authors: Solmaz, Ummuhan; Gumus, Ilkay; Yilmaz, Mustafa Kemal; Ince, Simay; Arslan, Hakan
• Is Part Of: Applied organometallic chemistry. Volume 35:Number 10(2021)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-07-15
• Subjects: benzoylthiourea -- catalytic activity -- crystal structure -- palladium complexes -- Suzuki C–C coupling reaction; Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.6348
• Languages: English
• ISSNs: 0268-2605

Abstract

Abstract: [PdCl2 (HL 1 ‐κS)2 ] and [PdCl2 (HL 2 ‐κS)2 ] complexes were formed from neutral monodentate modes of HL 1 and HL 2 ligands, which are coordinated to the palladium(II) center, respectively. [Pd(L 1 ‐κ 2 S, O)2 ] and [Pd(L 2 ‐κ 2 S, O)2 ] complexes were obtained by recrystallization of corresponding [PdCl2 (HL 1 ‐κS)2 ] and [PdCl2 (HL 2 ‐κS)2 ] complexes as anionic bidentate coordination modes. All palladium(II) complexes were characterized by elemental analysis, FT‐IR, and NMR ( 1 H and 13 C) techniques. The molecular structure of [Pd(L 1 ‐κ 2 S, O)2 ] and [Pd(L 2 ‐κ 2 S, O)2 ] was also confirmed by single‐crystal X‐ray diffraction method. The roles and behaviors of the prepared four palladium(II) complexes in catalytic investigations for the Suzuki C–C coupling reaction were examined for the first time. The complexes acted as the excellent catalyst precursor and showed highly catalytic activity for the Suzuki C–C coupling reaction of various arylhalides with phenylboronic acid at low catalyst loading (0.01 mol%). Abstract : [Pd(L‐κ 2 O, S)2 ] complex was obtained by recrystallization of [PdCl2 (HL‐κS)2 ] complex. The molecular structures of [Pd(L 1 ‐κ 2 S, O)2 ] and [Pd(L 2 ‐κ 2 S, O)2 ] complexes were confirmed by X‐ray diffraction analysis in single crystal. All palladium precursors performed excellent catalytic activity in the Suzuki C–C coupling reaction. Highlights: All compounds were structurally characterized by FT‐IR, 1 H NMR, and 13 C NMR spectroscopies. [Pd(L‐κ 2 O, S)2 ] complex was obtained by recrystallization of [PdCl2 (HL‐κS)2 ] complex. The molecular structures of [Pd(L 1 ‐κ 2 S, O)2 ] and [Pd(L 2 ‐κ 2 S, O)2 ] complexes were confirmed by X‐ray diffraction analysis in single crystal. The structure of the compounds was stabilized by hydrogen bond interactions. All palladium precursors performed excellent catalytic activity in the Suzuki C–C coupling reaction.